A0496000
Aminoglutethimide
European Pharmacopoeia (EP) Reference Standard
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Synonym(s):
DL-Aminoglutethimide, 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
Recommended Products
grade
pharmaceutical primary standard
API family
aminoglutethimide
manufacturer/tradename
EDQM
mp
152-154 °C (lit.)
application(s)
pharmaceutical (small molecule)
format
neat
storage temp.
2-8°C
SMILES string
CCC1(CCC(=O)NC1=O)c2ccc(N)cc2
InChI
1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
InChI key
ROBVIMPUHSLWNV-UHFFFAOYSA-N
Gene Information
human ... CYP11A1(1583) , CYP19A1(1588)
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General description
This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.
Application
Aminoglutethimide EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.
Biochem/physiol Actions
DL-Aminoglutethimide is a derivative of the sedative glutethimide. Originally introduced as an anticonvulsant, it was found to cause adrenal insufficiency. Blocks adrenal steroidogenesis by inhibiting the enzymatic conversion of cholesterol to pregnenolone. It also blocks the peripheral conversion (aromatization) of androgenic precursors to estrogens. The D-isomer is 30 times more potent at inhibiting aromatase activity, whereas the L-isomer is more potent at inhibiting cholesterol side-chain cleavage (steroidogenesis).
Packaging
The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.
Other Notes
Sales restrictions may apply.
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Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
监管及禁止进口产品
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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E Samojlik et al.
The Journal of clinical investigation, 65(3), 602-612 (1980-03-01)
We evaluated the comparative effects of aminoglutethimide (AG) on androgen and estrogen levels estrone ([E1], estradiol [E2], plasma dehydroepiandrosterone-sulfate [DHEA-S], testosterone [T], dihydrotestosterone [DHT], delta 4-androstenedione [delta 4-A]), follicle-stimulating hormone (FSH), luteinizing hormone (LH), and prolactin in postmenopausal patients with
M A Shaw et al.
Journal of steroid biochemistry, 31(1), 137-146 (1988-07-01)
Aminoglutethimide and ketoconazole, although originally developed as an anticonvulsant and antifungal agent respectively, have both been used to suppress steroid biosynthesis in patients with hormone-sensitive cancer. Aminoglutethimide inhibits several enzymes involved in the synthesis of corticosteroids as well as the
Adrenocortical steroidogenesis and aminoglutethimide I. Biomedical studies.
Y Touitou et al.
Biomedicine / [publiee pour l'A.A.I.C.I.G.], 18(3), 185-191 (1973-05-01)
A L Harris
Breast cancer research and treatment, 6(3), 201-211 (1985-01-01)
Could aminoglutethimide replace adrenalectomy? This question has already been answered in clinical practice in the United Kingdom, for surgical adrenalectomy has declined markedly in frequency as new hormonal therapy has appeared. An optimal assessment of an endocrine therapy can only
M Cikes
Schweizerische medizinische Wochenschrift, 113(11), 382-391 (1983-03-19)
The clinical profile of aminoglutethimide (AG), an amino derivative of the hypnotic agent glutethimide, is described. AG suppresses estrogen formation in postmenopausal women by its inhibitory effect on steroid synthesis in the adrenal glands as well as in the peripheral
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